Facile One-Pot Synthesis and Crystal Structure of 2:1 Adducts of Myrcene (or Ocimene) with Benzoquinones

Author(s): Sujata V. Bhat*, Rohan S. Pawar, P. Rajakannu

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 8 , 2020

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Graphical Abstract:


Abstract:

One-pot tandem oxidation and double Diels-Alder reaction of myrcene or ocimene with in situ generated 1,4-benzoquinone or 1,2-benzoquinone at 0°C for 1.5 h yielded polyalkylated 1,4,4a,5,8,8a,9a,10a-octahydro-9,10-anthracenediones and bis(alkylated) 9,10-phenanthrenedione respectively. The structure of novel bis-adduct from ocimene, (1R,4aR,5S,8aS,9aS,10aR)-rel- 1,4,4a,5,8,8a,9a,10a-octahydro-2,6-dimethyl-1,5-bis(3-methyl-2-buten-1-yl)-9,10-anthracenedione, was elucidated through single crystal X-ray analysis.

Keywords: Bis-adducts, Diels-Alder reaction, IBD, monoterpene conjugated dienes, polyalkylated 1, 4, 4a, 5, 8, 8a, 9a, 10aoctahydro- 9, 10-anthracenediones, bis(alkylated) 9, 10-phenanthrenedione, tandem oxidation.

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Article Details

VOLUME: 17
ISSUE: 8
Year: 2020
Page: [624 - 627]
Pages: 4
DOI: 10.2174/1570178617666200227110001
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